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Kajol mengawali 2000 dengan muncul dalam sebuah iklan [[Pepsi]], dan kembali menolak sebuah proyek—melodrama Aditya Chopra ''[[Mohabbatein]]''.<ref name="Rejected roles02" /><ref>{{Cite news|last=Patil|first=Vimla|author-link=Vimla Patil|date=16 September 2000|title=Superstar models or model superstars?|url=https://www.tribuneindia.com/2000/20000916/windows/main8.htm|work=The Tribune|archive-url=https://web.archive.org/web/20081006134838/https://www.tribuneindia.com/2000/20000916/windows/main8.htm|archive-date=6 Oktober 2008|access-date=17 Agustus 2020|url-status=live}}</ref> Ia memilih untuk tampil dengan suaminya dalam ''[[Raju Chacha]]'', salah satu film India termahal pada masanya.<ref>{{Cite web|date=7 November 2020|title=Raju Chacha may be most expensive Bollywood film ever|url=https://www.rediff.com/movies/2000/nov/08raju.htm|publisher=Rediff.com|archive-url=https://web.archive.org/web/20191208204542/https://www.rediff.com/movies/2000/nov/08raju.htm|archive-date=8 Desember 2019|access-date=12 Agustus 2020|url-status=live}}</ref> Kajol berperan sebagai Anna, seorang pengasuh bayi yang disukai oleh seorang penipu. Film tersebut gagal secara komersial, dan mendapatkan ulasan campuran para kritikus.<ref name="filmography" /> [[Taran Adarsh]] (dalam sebuah ulasan untuk [[Bollywood Hungama]]) menulis bahwa Kajol kelihatan "lebih lumayan dalam adegan-adegan dramatis",<ref>{{Cite web|last=Adarsh|first=Taran|authorlink=Taran Adarsh|date=30 Desember 2000|title=Raju Chacha: Movie Review|url=https://www.bollywoodhungama.com/movie/raju-chacha/critic-review/raju-chacha-movie-review/|publisher=Bollywood Hungama|archive-url=https://web.archive.org/web/20200812125541/https://www.bollywoodhungama.com/movie/raju-chacha/critic-review/raju-chacha-movie-review/|archive-date=12 Agustus 2020|access-date=12 Agustus 2020|url-status=live}}</ref> dan Aparajita Saha mengkritik perpaduan akting antara Kajol dengan Devgn.<ref>{{Cite web|last=Saha|first=Aparajita|date=29 Desember 2000|title=Reluctant heroine, reformed hero|url=https://www.rediff.com/movies/2000/dec/29raj.htm|publisher=Rediff.com|archive-url=https://web.archive.org/web/20030815004755/https://www.rediff.com/movies/2000/dec/29raj.htm|archive-date=15 Agustus 2003|access-date=12 Agustus 2020|url-status=live}}</ref> Pada tahun yang sama, ia melancurkan Cineexplore, sebuah portal web tentang aspek pembuatan film.<ref>{{Cite news|last=Choudhary, Anuradha|date=Desember 2000|title=Lights! Action! Kajol!|url=http://downloads.movies.indiatimes.com/site/dec2000/cs1.html|work=Filmfare|archive-url=https://web.archive.org/web/20131109165736/http://downloads.movies.indiatimes.com/site/dec2000/cs1.html|archive-date=9 November 2013|access-date=13 Agustus 2020|url-status=dead}}</ref>
 
''[[The Tribune (Chandigarh)|The Tribune]]'' menyebut ''[[Kuch Khatti Kuch Meethi]]'' (2001) sebagai "permulaan dari babak kedua" dalam karier Kajol.<ref name="The Tribune01">{{Cite news|last=Gupta|first=Rakhee|date=22 Februari 2001|title=Kajol decides to ‘phase out’|url=https://www.tribuneindia.com/2001/20010222/main8.htm|work=The Tribune|archive-url=https://web.archive.org/web/20191011212618/https://www.tribuneindia.com/2001/20010222/main8.htm|archive-date=11 Oktober 2019|access-date=13 Agustus 2020|url-status=live}}</ref> Baik film tersebut maupun penampilannya tidak ada yang ditanggapi secara positif;<ref name="filmography" /> Savera R. Someshwar mengkritik keputusan Kajol untuk membintangi film tersebut, menyebutnya hanya menjadi sebuah "alat bantu glamor" dan menggambarkan penampilannya "tidak menarik".<ref>{{Cite web|last=Someshwar|first=Savera R.|date=19 Januari 2001|title=Oh Kajol! Oh! Oh! Oh!&nbsp;– Kuch Khatti Kuch Meethi: Fills you deep... with despair|url=https://www.rediff.com/entertai/2001/jan/19khatti.htm|publisher=Rediff.com|archive-url=https://web.archive.org/web/20010128031200/https://www.rediff.com/entertai/2001/jan/19khatti.htm|archive-date=28 Januari 2001|access-date=13 Agustus 2020|url-status=live}}</ref> ''[[Kabhi Khushi Kabhie Gham...]]'', sebuah melodrama ansambel tahun 2001 [[Dharma Productions]] yang bertemakan nilai-nilai kekeluargaan, menjadi pengakhir kegagalan konsekutif tersebut.<ref>{{cite book |last=Mazumdar |first=Ranjani |year=2007 |url=https://books.google.co.id/books/about/Bombay_Cinema.html?id=xenNBrRKOGoC&printsec=frontcover&source=kp_read_button&redir_esc=y#v=onepage&q&f=false |title=Bombay Cinema: An Archive of the City |location=Minneapolis, Amerika Serikat |publisher=[[University of Minnesota Press]] |isbn=978-0-8166-4942-6 |pages=136–140 |access-date=13 Agustus 2020 }}</ref> Diproduksi dengan biaya sebesar {{INR}}400 juta,<ref>{{cite news|last=Dhawan |first=Himanshu |title=Look who's laughing |url=http://www.indiatoday.com/itoday/20020128/uk-cinema.shtml |work=India Today |date=28 Januari 2002 |access-date=11 September 2020 |url-status=dead |archive-url=https://web.archive.org/web/20150924034427/http://www.indiatoday.com/itoday/20020128/uk-cinema.shtml |archive-date=24 September 2015 }}</ref> film tersebut menempati peringkat [[Daftar film India berkeuntungan tertinggi di pasar luar negeri|film India berkeuntungan tertinggi di luar India]] selama lima tahun berturut-turut.<ref name="Overseas" /> Kajol ditunjuk sebagai pengganti Rani Mukerji untuk memerankan Anjali Sharma, sebuah peran yang mengharuskannya untuk mempelajari [[bahasa Punjab]].<ref>{{Cite news|last=Jha|first=Subhash K.|author-link=Subhash K. Jha|date=21 Desember 2001|title=Cherished moments in film-making|url=http://www.hindu.com/thehindu/fr/2001/12/21/stories/2001122100870300.htm|work=The Hindu|archive-url=https://web.archive.org/web/20120211170140/http://www.hindu.com/thehindu/fr/2001/12/21/stories/2001122100870300.htm|archive-date=11 Februari 2012|access-date=18 Agustus 2020|url-status=dead}}</ref><ref>{{Cite news|date=April 2002|title=Interview: Best Actress&nbsp;– Kajol|url=http://downloads.movies.indiatimes.com/site/april2002/ivw3.html|work=Filmfare|archive-url=https://web.archive.org/web/20140222165709/http://downloads.movies.indiatimes.com/site/april2002/ivw3.html|archive-date=22 Februari 2014|access-date=13 Agustus 2020|url-status=dead}}</ref> Penampilannya diulas secara campuran kritikus, dengan Anjum N. dari Rediff.com melihatnya "berlebihan",<ref>{{Cite web|last=N.|first=Anjum|date=14 Desember 2001|title=The Parent Trap: K3G is not about loving your parents only|url=https://www.rediff.com/entertai/2001/dec/14kabhi.htm|publisher=Rediff.com|archive-url=https://web.archive.org/web/20011215004519/https://www.rediff.com/entertai/2001/dec/14kabhi.htm|archive-date=15 Desember 2001|access-date=16 Agustus 2020|url-status=live}}</ref> sementara menulis untuk Bollywood Hungama, kritikus Taran Adarsh menulis bahwa Kajol menjadi "[bagian] terbaik", dan memuji dialek berbahasa Punjab-nya; namun, iatetapi berhasil untuk membuatnya meraih Penghargaan Filmfare dan Screen untuk Aktris Terbaik,<ref name="Awards01" /><ref>{{Cite web|last=Adarsh|first=Taran|date=11 Desember 2001|title=Kabhi Khushi Kabhie Gham: Movie Review|url=https://www.bollywoodhungama.com/movie/kabhi-khushi-kabhie-gham/critic-review/kabhi-khushi-kabhie-gham-movie-review/|publisher=Bollywood Hungama|archive-url=https://web.archive.org/web/20200520074357/https://www.bollywoodhungama.com/movie/kabhi-khushi-kabhie-gham/critic-review/kabhi-khushi-kabhie-gham-movie-review/|archive-date=20 Mei 2020|access-date=6 September 2020|url-status=live}}</ref> dan dinominasikan untuk [[Penghargaan IIFA untuk Aktris Terbaik|Akademi Film India Internasional]] (AFII)<ref>{{Cite news|last=Goodridge|first=Mike|date=15 Maret 2002|title=Lagaan, K3G battle it out for the Indian Int'l awards|url=https://www.screendaily.com/lagaan-k3g-battle-it-out-for-indian-intl-awards/408648.article|work=[[Screen International]]|archive-url=https://web.archive.org/web/20200714063629/https://www.screendaily.com/lagaan-k3g-battle-it-out-for-indian-intl-awards/408648.article|archive-date=14 Juli 2020|access-date=16 Agustus 2020|url-status=live}}</ref> dan Zee Cine.<ref>{{Cite web|last=Zee Entertainment Enteprises|title=Zee Cine Awards (ZCA) 2002&nbsp;– Winners and Nominees|url=https://www.zeecineawards.com/timeline/2002/winners/|publisher=Penghargaan Zee Cine|archive-url=https://web.archive.org/web/20200517012831/https://www.zeecineawards.com/timeline/2002/winners/|archive-date=17 Mei 2020|access-date=16 Agustus 2020|url-status=live}}</ref>
 
Setelah kesuksesan ''Kabhi Khushi Kabhie Gham...'', Kajol cuti dari akting untuk mengurusi keluarganya.<ref>{{Cite news|date=November 2001|title=In Focus: Gimme Gold|url=http://downloads.movies.indiatimes.com/site/nov2001/ifocus10.html|work=Filmfare|archive-url=https://web.archive.org/web/20131109222229/http://downloads.movies.indiatimes.com/site/nov2001/ifocus10.html|archive-date=9 Februari 2013|access-date=13 Agustus 2020|url-status=dead}}</ref> Ia juga dikabarkan tengah hamil pada masa produksi film tersebut, namun pada Desember 2001 ia [[keguguran]] setelah [[kehamilan ektopik|kehamilannya dinyatakan ektopik]];<ref>{{Cite news|last=Times News Network|date=21 Desember 2001|title=Kajol back home after miscarriage|url=https://timesofindia.indiatimes.com/calcutta-times/Kajol-back-home-after-miscarriage/articleshow/1836353123.cms|work=The Times of India|archive-url=https://web.archive.org/web/20191105062529/https://timesofindia.indiatimes.com/calcutta-times/Kajol-back-home-after-miscarriage/articleshow/1836353123.cms|archive-date=5 November 2019|access-date=13 Agustus 2020|url-status=live}}</ref> ia keguguran kembali setelahnya, namun tidak diketahui kapan hal tersebut terjadi.<ref>{{Cite news|last=India Today Web Desk|date=9 Januari 2020|title=Kajol opens up on miscarriages and life with Ajay Devgn: We’ve been through so much|url=https://www.indiatoday.in/movies/celebrities/story/kajol-opens-up-on-miscarriages-and-life-with-ajay-devgn-we-ve-been-through-so-much-1635243-2020-01-09|work=India Today|archive-url=https://web.archive.org/web/20200109132516/https://www.indiatoday.in/movies/celebrities/story/kajol-opens-up-on-miscarriages-and-life-with-ajay-devgn-we-ve-been-through-so-much-1635243-2020-01-09|archive-date=9 Januari 2020|access-date=16 Agustus 2020|url-status=live}}</ref> Sesudahnya, Kajol menolak lima proyek berturut-turut—''[[Gadar: Ek Prem Katha]]'', ''[[Devdas (film Hindi 2002)|Devdas]]'', ''[[Shakti: The Power]]'', ''[[Chalte Chalte (film 2003)|Chalte Chalte]]'', dan ''[[Veer-Zaara]]''—mengatakan: "Saya tidak suka sebagian besar film yang ditawarkan kepada saya [tersebut]."<ref name="Rejected roles01" /><ref name="Rejected roles02">{{Cite news|date=30 September 2010|title=Mr Smith, who do you think makes a better Mrs Smith?|url=https://www.telegraphindia.com/entertainment/mr-smith-who-do-you-think-makes-a-better-mrs-smith/cid/482087|work=The Telegraph|archive-url=https://archive.vn/Ao3wf|archive-date=26 Agustus 2020|access-date=26 Agustus 2020|url-status=live}}</ref><ref>{{Cite news|last=Kukreja|first=Monika Rawal|date=15 Juni 2017|title=16 years of Gadar: The Sunny Deol-Ameesha Patel film was written for Govinda and Kajol|url=https://www.hindustantimes.com/bollywood/16-years-of-gadar-the-sunny-deol-ameesha-patel-film-was-written-for-govinda-and-kajol/story-gqhNCm9hrbBBVX7voEoYoJ.html|work=Hindustan Times|archive-url=https://web.archive.org/web/20180101081712/https://www.hindustantimes.com/bollywood/16-years-of-gadar-the-sunny-deol-ameesha-patel-film-was-written-for-govinda-and-kajol/story-gqhNCm9hrbBBVX7voEoYoJ.html|archive-date=1 Januari 2018|access-date=27 Agustus 2020|url-status=live}}</ref><ref>{{Cite web|last=Rediff Entertainment Bureau|date=27 Januari 2000|title=Babita, Kareena eat humble pie|url=https://m.rediff.com/entertai/2000/jan/27inside.htm|publisher=Rediff.com|archive-url=https://archive.vn/6iD3Y|archive-date=26 Agustus 2020|access-date=26 Agustus 2020|url-status=live}}</ref> Pada April 2003, ia melahirkan anak pertamanya Nysa di [[Rumah Sakit Breach Candy]].<ref>{{Cite news|last=Press Trust of India|date=20 April 2003|title=Kajol delivers baby girl|url=http://articles.timesofindia.indiatimes.com/2003-04-20/news-interviews/27274297_1_baby-girl-kajol-first-child|work=The Times of India|archive-url=https://web.archive.org/web/20131002172623/http://articles.timesofindia.indiatimes.com/2003-04-20/news-interviews/27274297_1_baby-girl-kajol-first-child|archive-date=2 Oktober 2013|access-date=13 Agustus 2020|url-status=dead}}</ref>